Ethylparaben → HCID 19834221, compound

HRID 2050989Notes

Reaction equation

HRID 2050989 reaction equation
[CH3:1][C:2]1([CH3:16])[C:11]2[C:6](=[CH:7][C:8]([CH3:15])=[C:9]([C:12]([OH:14])=[O:13])[CH:10]=2)[S:5][CH2:4][CH2:3]1.[CH2:17]([O:19][C:20](=[O:28])[C:21]1[CH:26]=[CH:25][C:24](O)=[CH:23][CH:22]=1)[CH3:18].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:1][C:2]1([CH3:16])[C:11]2[C:6](=[CH:7][C:8]([CH3:15])=[C:9]([C:12]([O:14][C:24]3[CH:25]=[CH:26][C:21]([C:20]([O:19][CH2:17][CH3:18])=[O:28])=[CH:22][CH:23]=3)=[O:13])[CH:10]=2)[S:5][CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 8434EthylparabenHCID 10868DicyclohexylcarbodiimideHCID 18989941HCID 18989941, compound

Product 1

HCID 19834221HCID 19834221, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 83.7 mg (0.35 mmol) of 4,4,7-trimethyl-6-carboxythiochroman and 59.1 mg (0.35 mmol) of ethyl-4-hydroxybenzoate in 2 ml of methylene chloride was treated sequentially with 74.5 mg (0.36 mmol) of 1,3-dicyclohexylcarbodiimide and 11.1 mg (0.09 mmol) of 4-dimethylaminopyridine. The mixture was stirred under nitrogen for 24 h and then filtered. The fillrate was concentrated in-vacuo and the residue purified by flash chromatography (silica; 15% ethyl acetate in henane) to give the title compound as a pale yellow oil. PMR (CDCl3): δ1.37 (6H, s), 1.41 (3H, t, J~7.1 Hz), 1.92-2.00 (2H, m), 2.56 (3H, s), 3.02-3.10 (2H, m), 4.40 (2H, q, J~7.1 Hz), 7.03 (1H, s), 7.29 (2H, d, J~8.7 Hz), 8.13 (2H, d, J~8.7 Hz), 8.18 (1H, s).

Workup

  1. filtrationfiltered
  2. concentrationThe fillrate was concentrated in-vacuo
  3. customthe residue purified by flash chromatography (silica; 15% ethyl acetate in henane)

Sources & evidence

ORD record
ord-e1e915c6113d4099a40e400d5bbe35c9
Source dataset
uspto-grants-1991_05
Patent number
US05015658

Reaction notes

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